反応 #577220

反応方程式

7-Allyloxy-4-methylcoumarin

N,N-diethylaniline

→

3

収率 88.0%

8-Allyl-7-hydroxyl-4-methyl-2H-chromen-2-one

収率 88.0%

反応条件

後処理

1. 1
   温度The reaction mixture was then cooled, during which some of the product
2. 2
   その他precipitated
3. 3
   workup.ADDITIONHexane (10 mL) was added in order
4. 4
   その他to precipitate out the remaining product
5. 5
   ろ過The precipitate was filtered
6. 6
   洗浄washed with hexane
7. 7
   その他dried under vacuum

実験手順

7-Allyloxy-4-methylcoumarin 2 (1.0 g, 4.62 mmol) was dissolved in N,N-diethylaniline (8 mL) in a sealed vial and heated to 250° C. for 25 min under microwave. The reaction mixture was then cooled, during which some of the product precipitated. Hexane (10 mL) was added in order to precipitate out the remaining product. The precipitate was filtered, washed with hexane, and dried under vacuum to yield 3 as a pale-yellow solid (0.88 g, 88%). TLC (hexane/ethyl acetate, 1:3): Rf=0.5. mp 204° C. 1H NMR (CDCl3/CD3OD, 500 MHz) δ 2.43 (s, 3H, CH3), 3.57 (d, J=6.0 Hz, 2H, CH2), 4.95 (d, J=10.0 Hz, 1H), 5.04 (d, J=17.0 Hz, 1H), 5.97 (m, 1H), 6.10 (s, 1H), 6.86 (d, J=9.0 Hz, 1H), 7.46 (d, J=9.0 Hz, 1H). 13C NMR (CDCl3/CD3OD, 125 MHz) δ 18.85, 27.66, 110.78, 113.20, 113.73, 114.93, 115.41, 124.38, 136.16, 153.89, 155.88, 160.18, 163.92. ESIMS calcd for C13H13O3 [M+H]+ 217.1. Found 217.2.

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